NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	152.08
Volume:	165.335
LogP:	1.812
LogD:	1.745
LogS:	-1.233
# Rotatable Bonds:	2
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.521
Synthetic Accessibility Score:	2.142
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.159
MDCK Permeability:	2.6993318897439167e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.099
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.587
Plasma Protein Binding (PPB):	88.34507751464844%
Volume Distribution (VD):	3.287
Pgp-substrate:	14.84230899810791%

ADMET: Metabolism

CYP1A2-inhibitor:	0.434
CYP1A2-substrate:	0.26
CYP2C19-inhibitor:	0.116
CYP2C19-substrate:	0.786
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.328
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.528
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.29

ADMET: Excretion

Clearance (CL):	5.857
Half-life (T1/2):	0.66

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.872
Rat Oral Acute Toxicity:	0.732
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.607
Carcinogencity:	0.734
Eye Corrosion:	0.979
Eye Irritation:	0.994
Respiratory Toxicity:	0.968

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC328178

Natural Product ID:	NPC328178
*Common Name:**	Cumene Hydroperoxide
IUPAC Name:	2-hydroperoxypropan-2-ylbenzene
Synonyms:	Cumene Hydroperoxide
Standard InCHIKey:	YQHLDYVWEZKEOX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H12O2/c1-9(2,11-10)8-6-4-3-5-7-8/h3-7,10H,1-2H3
SMILES:	OOC(c1ccccc1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1518369
PubChem CID:	6629
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002811] Phenylpropanes

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30193	Mycoplasma genitalium	Species	Mycoplasmataceae	Bacteria	n.a.	n.a.	n.a.	PMID[22817898]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1
Potency	46

Activity Type	# Activity
Cell Line	21
Individual Protein	10
Others	16

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	79432.8	nM	PMID[575423]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	39810.7	nM	PMID[575423]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	50118.7	nM	PMID[575423]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	1584.9	nM	PMID[575423]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PMID[575423]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	25118.9	nM	PMID[575423]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	31622.8	nM	PMID[575423]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	63095.7	nM	PMID[575423]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[575425]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[575423]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[575423]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	64.0	%	PMID[575427]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	188.3	nM	PMID[575423]
NPT103	Individual Protein	Nuclear receptor ROR-gamma	Homo sapiens	Potency	n.a.	42163.2	nM	PMID[575423]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[575423]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	125.9	nM	PMID[575423]
NPT610	Others	Molecular identity unknown		Potency	n.a.	66824.2	nM	PMID[575423]
NPT2	Others	Unspecified		Potency	n.a.	61644.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	30637.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	17228.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43641.2	nM	PubChem BioAssay data set

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC328178 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	2045
0.2-0.3	5822
0.3-0.4	14537
0.4-0.5	12514
0.5-0.6	5710
0.6-0.7	1490
0.7-0.8	311
0.8-0.85	14
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9351	High Similarity	NPC133050
0.9241	High Similarity	NPC95429
0.9012	High Similarity	NPC474211
0.9	High Similarity	NPC168855
0.8889	High Similarity	NPC474354
0.8816	High Similarity	NPC189371
0.869	High Similarity	NPC1793
0.8537	High Similarity	NPC304538
0.8519	High Similarity	NPC99394
0.8519	High Similarity	NPC87299
0.8519	High Similarity	NPC329319
0.8519	High Similarity	NPC103326
0.8415	Intermediate Similarity	NPC172984
0.8395	Intermediate Similarity	NPC117180
0.8333	Intermediate Similarity	NPC93843
0.825	Intermediate Similarity	NPC224544
0.8125	Intermediate Similarity	NPC66655
0.8072	Intermediate Similarity	NPC106313
0.7978	Intermediate Similarity	NPC306074
0.7978	Intermediate Similarity	NPC304541
0.7976	Intermediate Similarity	NPC477770
0.7975	Intermediate Similarity	NPC108218
0.7955	Intermediate Similarity	NPC318325
0.7955	Intermediate Similarity	NPC242240
0.7955	Intermediate Similarity	NPC123273
0.7955	Intermediate Similarity	NPC258219
0.7931	Intermediate Similarity	NPC304760
0.7931	Intermediate Similarity	NPC23167
0.7931	Intermediate Similarity	NPC407
0.7931	Intermediate Similarity	NPC307235
0.7889	Intermediate Similarity	NPC55903
0.7865	Intermediate Similarity	NPC79917
0.7841	Intermediate Similarity	NPC27974
0.7841	Intermediate Similarity	NPC199567
0.7841	Intermediate Similarity	NPC25493
0.7841	Intermediate Similarity	NPC113460
0.7816	Intermediate Similarity	NPC197783
0.7816	Intermediate Similarity	NPC155393
0.7802	Intermediate Similarity	NPC27323
0.7802	Intermediate Similarity	NPC316301
0.7802	Intermediate Similarity	NPC289769
0.7802	Intermediate Similarity	NPC152415
0.7791	Intermediate Similarity	NPC58616
0.7778	Intermediate Similarity	NPC45040
0.7778	Intermediate Similarity	NPC155908
0.7766	Intermediate Similarity	NPC72729
0.7753	Intermediate Similarity	NPC280347
0.7753	Intermediate Similarity	NPC177420
0.7738	Intermediate Similarity	NPC242628
0.7738	Intermediate Similarity	NPC165212
0.7722	Intermediate Similarity	NPC208302
0.7717	Intermediate Similarity	NPC8392
0.7717	Intermediate Similarity	NPC26244
0.7711	Intermediate Similarity	NPC170484
0.7701	Intermediate Similarity	NPC175313
0.7701	Intermediate Similarity	NPC248817
0.7701	Intermediate Similarity	NPC286904
0.7701	Intermediate Similarity	NPC243166
0.7692	Intermediate Similarity	NPC94139
0.7692	Intermediate Similarity	NPC325292
0.7692	Intermediate Similarity	NPC138117
0.7692	Intermediate Similarity	NPC3358
0.7692	Intermediate Similarity	NPC210497
0.7692	Intermediate Similarity	NPC162314
0.7692	Intermediate Similarity	NPC147284
0.7692	Intermediate Similarity	NPC271440
0.7692	Intermediate Similarity	NPC306884
0.7684	Intermediate Similarity	NPC154905
0.7684	Intermediate Similarity	NPC60373
0.7667	Intermediate Similarity	NPC192
0.7667	Intermediate Similarity	NPC300017
0.7667	Intermediate Similarity	NPC55561
0.766	Intermediate Similarity	NPC92730
0.7634	Intermediate Similarity	NPC259512
0.7634	Intermediate Similarity	NPC312132
0.7634	Intermediate Similarity	NPC473388
0.7619	Intermediate Similarity	NPC121800
0.7614	Intermediate Similarity	NPC198747
0.7614	Intermediate Similarity	NPC211237
0.7614	Intermediate Similarity	NPC89377
0.7614	Intermediate Similarity	NPC322387
0.7609	Intermediate Similarity	NPC128062
0.7609	Intermediate Similarity	NPC245187
0.7609	Intermediate Similarity	NPC151715
0.7604	Intermediate Similarity	NPC19856
0.7586	Intermediate Similarity	NPC265146
0.7586	Intermediate Similarity	NPC124436
0.7586	Intermediate Similarity	NPC99482
0.7582	Intermediate Similarity	NPC204210
0.7582	Intermediate Similarity	NPC128645
0.7582	Intermediate Similarity	NPC270547
0.7579	Intermediate Similarity	NPC469481
0.7556	Intermediate Similarity	NPC70436
0.7553	Intermediate Similarity	NPC474073
0.7553	Intermediate Similarity	NPC225464
0.7553	Intermediate Similarity	NPC79241
0.7553	Intermediate Similarity	NPC6597
0.7553	Intermediate Similarity	NPC77492
0.7528	Intermediate Similarity	NPC184169
0.7527	Intermediate Similarity	NPC222146
0.7527	Intermediate Similarity	NPC21959
0.7527	Intermediate Similarity	NPC274678
0.7527	Intermediate Similarity	NPC313650
0.7527	Intermediate Similarity	NPC144682
0.7526	Intermediate Similarity	NPC315794
0.75	Intermediate Similarity	NPC150837
0.7474	Intermediate Similarity	NPC33675
0.7474	Intermediate Similarity	NPC128723
0.7474	Intermediate Similarity	NPC252821
0.7474	Intermediate Similarity	NPC299762
0.7474	Intermediate Similarity	NPC122005
0.7467	Intermediate Similarity	NPC135924
0.7449	Intermediate Similarity	NPC471133
0.7447	Intermediate Similarity	NPC292730
0.7447	Intermediate Similarity	NPC216520
0.7447	Intermediate Similarity	NPC82664
0.7447	Intermediate Similarity	NPC132271
0.7444	Intermediate Similarity	NPC19680
0.7444	Intermediate Similarity	NPC220893
0.7444	Intermediate Similarity	NPC173443
0.7444	Intermediate Similarity	NPC104216
0.7442	Intermediate Similarity	NPC323103
0.7442	Intermediate Similarity	NPC73637
0.7442	Intermediate Similarity	NPC283012
0.7442	Intermediate Similarity	NPC103387
0.7442	Intermediate Similarity	NPC121478
0.7442	Intermediate Similarity	NPC475199
0.7423	Intermediate Similarity	NPC108497
0.7419	Intermediate Similarity	NPC76938
0.7412	Intermediate Similarity	NPC164449
0.7412	Intermediate Similarity	NPC184030
0.7412	Intermediate Similarity	NPC192623
0.7396	Intermediate Similarity	NPC225506
0.7396	Intermediate Similarity	NPC48730
0.7396	Intermediate Similarity	NPC248396
0.7396	Intermediate Similarity	NPC289117
0.7396	Intermediate Similarity	NPC129373
0.7396	Intermediate Similarity	NPC174911
0.7391	Intermediate Similarity	NPC231150
0.7391	Intermediate Similarity	NPC314690
0.7391	Intermediate Similarity	NPC321956
0.7374	Intermediate Similarity	NPC310456
0.7374	Intermediate Similarity	NPC53740
0.7368	Intermediate Similarity	NPC475078
0.7368	Intermediate Similarity	NPC152097
0.7368	Intermediate Similarity	NPC229242
0.7368	Intermediate Similarity	NPC29680
0.7368	Intermediate Similarity	NPC260000
0.7363	Intermediate Similarity	NPC70940
0.7363	Intermediate Similarity	NPC98772
0.7363	Intermediate Similarity	NPC86670
0.7363	Intermediate Similarity	NPC274455
0.7356	Intermediate Similarity	NPC288903
0.7356	Intermediate Similarity	NPC146703
0.7356	Intermediate Similarity	NPC270507
0.7356	Intermediate Similarity	NPC285773
0.7347	Intermediate Similarity	NPC120719
0.7347	Intermediate Similarity	NPC475225
0.7347	Intermediate Similarity	NPC475580
0.7342	Intermediate Similarity	NPC82770
0.7342	Intermediate Similarity	NPC78954
0.7342	Intermediate Similarity	NPC239931
0.734	Intermediate Similarity	NPC32714
0.7333	Intermediate Similarity	NPC329064
0.732	Intermediate Similarity	NPC51015
0.732	Intermediate Similarity	NPC300166
0.732	Intermediate Similarity	NPC25458
0.732	Intermediate Similarity	NPC252105
0.732	Intermediate Similarity	NPC304873
0.732	Intermediate Similarity	NPC12221
0.7312	Intermediate Similarity	NPC181709
0.7312	Intermediate Similarity	NPC29373
0.73	Intermediate Similarity	NPC472980
0.73	Intermediate Similarity	NPC472979
0.73	Intermediate Similarity	NPC66834
0.73	Intermediate Similarity	NPC27252
0.7297	Intermediate Similarity	NPC212114
0.7297	Intermediate Similarity	NPC120441
0.7297	Intermediate Similarity	NPC300345
0.7297	Intermediate Similarity	NPC65873
0.7294	Intermediate Similarity	NPC469894
0.7292	Intermediate Similarity	NPC217621
0.7292	Intermediate Similarity	NPC132078
0.7292	Intermediate Similarity	NPC280869
0.7292	Intermediate Similarity	NPC260775
0.7292	Intermediate Similarity	NPC216468
0.7292	Intermediate Similarity	NPC51333
0.7292	Intermediate Similarity	NPC78119
0.7292	Intermediate Similarity	NPC100870
0.7292	Intermediate Similarity	NPC80027
0.7283	Intermediate Similarity	NPC300478
0.7283	Intermediate Similarity	NPC47950
0.7283	Intermediate Similarity	NPC71853
0.7283	Intermediate Similarity	NPC312304
0.7273	Intermediate Similarity	NPC138942
0.7273	Intermediate Similarity	NPC88566
0.7273	Intermediate Similarity	NPC47284
0.7263	Intermediate Similarity	NPC202986
0.7263	Intermediate Similarity	NPC325499
0.7245	Intermediate Similarity	NPC71002

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC328178 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	1129
0.2-0.3	1377
0.3-0.4	3181
0.4-0.5	1926
0.5-0.6	971
0.6-0.7	269
0.7-0.8	38
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8125	Intermediate Similarity	NPD9294	Approved
0.7889	Intermediate Similarity	NPD845	Approved
0.7802	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD9250	Approved
0.7717	Intermediate Similarity	NPD2859	Approved
0.7717	Intermediate Similarity	NPD2860	Approved
0.766	Intermediate Similarity	NPD3020	Approved
0.7634	Intermediate Similarity	NPD288	Approved
0.7609	Intermediate Similarity	NPD2934	Approved
0.7609	Intermediate Similarity	NPD2933	Approved
0.7586	Intermediate Similarity	NPD111	Approved
0.7579	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD1616	Discontinued
0.7528	Intermediate Similarity	NPD1101	Approved
0.7527	Intermediate Similarity	NPD1809	Phase 2
0.7527	Intermediate Similarity	NPD844	Approved
0.75	Intermediate Similarity	NPD4817	Approved
0.75	Intermediate Similarity	NPD4818	Approved
0.7416	Intermediate Similarity	NPD1087	Approved
0.7391	Intermediate Similarity	NPD159	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD1089	Approved
0.7363	Intermediate Similarity	NPD1086	Approved
0.7363	Intermediate Similarity	NPD1090	Approved
0.7356	Intermediate Similarity	NPD9491	Approved
0.7333	Intermediate Similarity	NPD531	Approved
0.732	Intermediate Similarity	NPD846	Approved
0.732	Intermediate Similarity	NPD940	Approved
0.7294	Intermediate Similarity	NPD9490	Approved
0.7283	Intermediate Similarity	NPD530	Approved
0.7253	Intermediate Similarity	NPD800	Approved
0.7245	Intermediate Similarity	NPD4229	Approved
0.7245	Intermediate Similarity	NPD4658	Approved
0.7245	Intermediate Similarity	NPD3680	Approved
0.7245	Intermediate Similarity	NPD4656	Approved
0.7245	Intermediate Similarity	NPD3682	Approved
0.7245	Intermediate Similarity	NPD3683	Approved
0.7245	Intermediate Similarity	NPD4231	Approved
0.7245	Intermediate Similarity	NPD3681	Approved
0.7245	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1693	Approved
0.7216	Intermediate Similarity	NPD3028	Approved
0.7204	Intermediate Similarity	NPD1088	Approved
0.7204	Intermediate Similarity	NPD752	Approved
0.7188	Intermediate Similarity	NPD9612	Approved
0.7188	Intermediate Similarity	NPD9609	Approved
0.7188	Intermediate Similarity	NPD9611	Approved
0.7188	Intermediate Similarity	NPD9495	Approved
0.7176	Intermediate Similarity	NPD225	Approved
0.7176	Intermediate Similarity	NPD227	Approved
0.7128	Intermediate Similarity	NPD720	Approved
0.7128	Intermediate Similarity	NPD1202	Approved
0.7128	Intermediate Similarity	NPD719	Approved
0.7128	Intermediate Similarity	NPD1409	Phase 3
0.7126	Intermediate Similarity	NPD226	Approved
0.7111	Intermediate Similarity	NPD9259	Approved
0.7111	Intermediate Similarity	NPD9257	Approved
0.7097	Intermediate Similarity	NPD1239	Approved
0.7065	Intermediate Similarity	NPD9249	Phase 1
0.7051	Intermediate Similarity	NPD675	Discontinued
0.7041	Intermediate Similarity	NPD2555	Approved
0.7041	Intermediate Similarity	NPD2553	Approved
0.7041	Intermediate Similarity	NPD2552	Approved
0.7041	Intermediate Similarity	NPD2550	Approved
0.7041	Intermediate Similarity	NPD2558	Approved
0.7041	Intermediate Similarity	NPD2549	Approved
0.7037	Intermediate Similarity	NPD9497	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD9538	Approved
0.703	Intermediate Similarity	NPD1445	Approved
0.703	Intermediate Similarity	NPD1444	Approved
0.7024	Intermediate Similarity	NPD9716	Approved
0.7	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1237	Approved
0.7	Intermediate Similarity	NPD3047	Approved
0.7	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3048	Approved
0.7	Intermediate Similarity	NPD3046	Approved
0.699	Remote Similarity	NPD5239	Approved
0.699	Remote Similarity	NPD3021	Approved
0.699	Remote Similarity	NPD3022	Approved
0.699	Remote Similarity	NPD5240	Approved
0.699	Remote Similarity	NPD5236	Approved
0.699	Remote Similarity	NPD5237	Approved
0.699	Remote Similarity	NPD5235	Approved
0.6989	Remote Similarity	NPD9256	Approved
0.6989	Remote Similarity	NPD9258	Approved
0.697	Remote Similarity	NPD855	Approved
0.697	Remote Similarity	NPD4188	Approved
0.697	Remote Similarity	NPD4189	Approved
0.697	Remote Similarity	NPD854	Approved
0.6966	Remote Similarity	NPD3971	Phase 1
0.6947	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1563	Approved
0.6939	Remote Similarity	NPD2066	Phase 3
0.6923	Remote Similarity	NPD4254	Approved
0.6923	Remote Similarity	NPD2201	Approved
0.6923	Remote Similarity	NPD4253	Approved
0.6907	Remote Similarity	NPD1564	Approved
0.6907	Remote Similarity	NPD1565	Approved
0.6907	Remote Similarity	NPD1566	Phase 3
0.6893	Remote Similarity	NPD4720	Approved
0.6893	Remote Similarity	NPD4717	Approved
0.6893	Remote Similarity	NPD2684	Approved
0.6893	Remote Similarity	NPD4718	Approved
0.6887	Remote Similarity	NPD2228	Approved
0.6887	Remote Similarity	NPD2229	Approved
0.6887	Remote Similarity	NPD2234	Approved
0.6882	Remote Similarity	NPD5346	Phase 2
0.6882	Remote Similarity	NPD5347	Phase 2
0.6875	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2500	Approved
0.6857	Remote Similarity	NPD2499	Approved
0.6857	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4793	Discontinued
0.6832	Remote Similarity	NPD310	Approved
0.6832	Remote Similarity	NPD309	Approved
0.6832	Remote Similarity	NPD314	Approved
0.6832	Remote Similarity	NPD315	Approved
0.6832	Remote Similarity	NPD9608	Approved
0.6832	Remote Similarity	NPD9610	Approved
0.6832	Remote Similarity	NPD10	Approved
0.6832	Remote Similarity	NPD164	Approved
0.6832	Remote Similarity	NPD311	Approved
0.6827	Remote Similarity	NPD4750	Phase 3
0.6827	Remote Similarity	NPD1792	Phase 2
0.6822	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3673	Approved
0.6809	Remote Similarity	NPD3672	Approved
0.6804	Remote Similarity	NPD1989	Approved
0.6796	Remote Similarity	NPD2342	Discontinued
0.6792	Remote Similarity	NPD7635	Approved
0.6792	Remote Similarity	NPD1138	Approved
0.6768	Remote Similarity	NPD9712	Approved
0.6762	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4198	Discontinued
0.6735	Remote Similarity	NPD1875	Phase 1
0.6733	Remote Similarity	NPD1930	Approved
0.6733	Remote Similarity	NPD1415	Approved
0.6733	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD1929	Approved
0.6731	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD9087	Approved
0.6701	Remote Similarity	NPD4814	Discontinued
0.6701	Remote Similarity	NPD3772	Phase 3
0.67	Remote Similarity	NPD1242	Phase 1
0.6699	Remote Similarity	NPD3524	Approved
0.6699	Remote Similarity	NPD2559	Approved
0.6699	Remote Similarity	NPD3526	Approved
0.6699	Remote Similarity	NPD2551	Approved
0.6698	Remote Similarity	NPD1139	Approved
0.6698	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD1137	Approved
0.6667	Remote Similarity	NPD5909	Discontinued
0.6667	Remote Similarity	NPD475	Phase 2
0.6667	Remote Similarity	NPD9273	Approved
0.6667	Remote Similarity	NPD497	Approved
0.6667	Remote Similarity	NPD9710	Approved
0.6667	Remote Similarity	NPD5451	Approved
0.6667	Remote Similarity	NPD1282	Approved
0.6667	Remote Similarity	NPD9251	Approved
0.6667	Remote Similarity	NPD9711	Approved
0.6636	Remote Similarity	NPD7843	Approved
0.6635	Remote Similarity	NPD9532	Phase 3
0.6635	Remote Similarity	NPD290	Approved
0.6635	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4719	Phase 2
0.6606	Remote Similarity	NPD6671	Approved
0.6606	Remote Similarity	NPD7157	Approved
0.66	Remote Similarity	NPD1238	Approved
0.6598	Remote Similarity	NPD3719	Approved
0.6598	Remote Similarity	NPD3718	Approved
0.6591	Remote Similarity	NPD9088	Approved
0.6577	Remote Similarity	NPD7741	Discontinued
0.6574	Remote Similarity	NPD495	Approved
0.6574	Remote Similarity	NPD2991	Approved
0.6574	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD496	Approved
0.6574	Remote Similarity	NPD2988	Approved
0.6574	Remote Similarity	NPD5283	Phase 1
0.6574	Remote Similarity	NPD498	Approved
0.6571	Remote Similarity	NPD2182	Approved
0.6569	Remote Similarity	NPD6647	Phase 2
0.6569	Remote Similarity	NPD9500	Approved
0.6569	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD228	Approved
0.6538	Remote Similarity	NPD810	Approved
0.6538	Remote Similarity	NPD968	Approved
0.6538	Remote Similarity	NPD811	Approved
0.6538	Remote Similarity	NPD812	Approved
0.6531	Remote Similarity	NPD9260	Approved
0.6518	Remote Similarity	NPD4105	Approved
0.6518	Remote Similarity	NPD4102	Approved
0.6514	Remote Similarity	NPD1793	Approved
0.6514	Remote Similarity	NPD1791	Approved
0.6514	Remote Similarity	NPD2629	Approved
0.6514	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5951	Approved
0.6509	Remote Similarity	NPD9380	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data